tert-butyl (1S,3S,5S,6S)-6-((S)-2-((tert-butoxy)carbonylamino)propanamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylate | 1446762-78-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (1S,3S,5S,6S)-6-((S)-2-((tert-butoxy)carbonylamino)propanamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylate
• 英文别名: tert-butyl (1S,3S,6S,7S)-3-methyl-6-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-5-oxo-1-phenyl-7-propan-2-yl-1,2,6,7-tetrahydropyrazolo[1,2-a]pyrazole-3-carboxylate
• CAS: 1446762-78-2
• 化学式: C₂₉H₄₄N₄O₆
• 分子量: 544.692
• InChiKey: UAHLVNYBJQFYQM-XKKSFHEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl (1R,3R,5R,6R)-6-(benzyloxycarbonylamino)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、350.01 kPa 条件下， 反应 24.0h， 生成 tert-butyl (1S,3S,5S,6S)-6-((S)-2-((tert-butoxy)carbonylamino)propanamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylate 、 tert-butyl (1R,3R,5R,6R)-6-((S)-2-((tert-butoxy)carbonylamino)propanamido)-5-isopropyl-1-methyl-7-oxo-3-phenylhexahydropyrazolo[1,2-a]pyrazole-1-carboxylate
  参考文献：
  名称：

  Synthesis of pyrazolo[1,2-a]pyrazole-based peptide mimetics

  摘要：

  The synthesis of U-shaped conformationally constrained analogues of peptides based on the 3-amino-2oxo-1,5-diazabicyclo[3.3.0]octane-8-carboxylic acid scaffold was developed. [3+2] Cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4-benzyloxycarbonylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides to tert-butyl acrylate and tert-butyl methacrylate gave the corresponding racemic cycloadducts, in most cases as mixtures of isomers, which were separated by preparative chromatography. Selective deprotection of the C- and the N-terminal of these heterocyclic dipeptides followed by coupling with (S)-alanine derivatives and chromatographic separation furnished the non-racemic tripeptides as target compounds. The structures of racemic cycloadducts and non-racemic final products were determined by NMR spectroscopy and X-ray diffraction. The synthesized compounds were also evaluated for inhibition of MurD ligase and D-alanine:D-alanine ligase. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.122